Guitarist Eddie Lang used music to navigate the complexities of race and ethnicity in the 1920s. Like most musicians, he was caught in “the minstrel cycle,” which typically had three phases. It began with white Americans appropriating African American culture in order to ridicule it. In stage two, African American performers reappropriated minstrel stereotypes for their own uses. In stage three, minstrel stereotypes were re-imagined as forms of racial authenticity. This article revises the trajectory of jazz and blues by rooting it in the commercial play of the minstrel cycle, rather than in folk authenticity. It ends by comparing Lang to Charlie Christian, who found a way to escape the minstrel cycle altogether.